Formal total synthesis of aspergillide A

Yuko Izuchi, Nobuhiro Kanomata, Hiroyuki Koshino, Yayoi Hongo, Tadashi Nakata, Shunya Takahashi

    Research output: Contribution to journalArticle

    21 Citations (Scopus)

    Abstract

    The formal total synthesis of aspergillide A 1 is described. The cross-metathesis of enone 6 with 6-hepten-2-ol derivative 5 provided E-olefin 15 corresponding to the C4-C14 backbone of 1. The CBS asymmetric reduction of 15 gave allyl alcohol 16, which was transformed into β-alkoxyacrylate 4 which had a formyl group. SmI2-induced reductive cyclization of 4 gave a 2,6-syn-2,3-trans THP derivative 3 in good yield. After methoxymethylation of 3, the resulting compound 19 was submitted to desilylation and hydrolysis, to afford Fuwa's key intermediate 2 for the total synthesis of 1.

    Original languageEnglish
    Pages (from-to)246-251
    Number of pages6
    JournalTetrahedron Asymmetry
    Volume22
    Issue number2
    DOIs
    Publication statusPublished - 2011 Jan 31

    Fingerprint

    Derivatives
    metathesis
    Cyclization
    Alkenes
    synthesis
    alkenes
    Olefins
    hydrolysis
    Hydrolysis
    alcohols
    Alcohols
    aspergillide A
    allyl alcohol

    ASJC Scopus subject areas

    • Organic Chemistry
    • Inorganic Chemistry
    • Physical and Theoretical Chemistry
    • Catalysis

    Cite this

    Izuchi, Y., Kanomata, N., Koshino, H., Hongo, Y., Nakata, T., & Takahashi, S. (2011). Formal total synthesis of aspergillide A. Tetrahedron Asymmetry, 22(2), 246-251. https://doi.org/10.1016/j.tetasy.2011.01.016

    Formal total synthesis of aspergillide A. / Izuchi, Yuko; Kanomata, Nobuhiro; Koshino, Hiroyuki; Hongo, Yayoi; Nakata, Tadashi; Takahashi, Shunya.

    In: Tetrahedron Asymmetry, Vol. 22, No. 2, 31.01.2011, p. 246-251.

    Research output: Contribution to journalArticle

    Izuchi, Y, Kanomata, N, Koshino, H, Hongo, Y, Nakata, T & Takahashi, S 2011, 'Formal total synthesis of aspergillide A', Tetrahedron Asymmetry, vol. 22, no. 2, pp. 246-251. https://doi.org/10.1016/j.tetasy.2011.01.016
    Izuchi Y, Kanomata N, Koshino H, Hongo Y, Nakata T, Takahashi S. Formal total synthesis of aspergillide A. Tetrahedron Asymmetry. 2011 Jan 31;22(2):246-251. https://doi.org/10.1016/j.tetasy.2011.01.016
    Izuchi, Yuko ; Kanomata, Nobuhiro ; Koshino, Hiroyuki ; Hongo, Yayoi ; Nakata, Tadashi ; Takahashi, Shunya. / Formal total synthesis of aspergillide A. In: Tetrahedron Asymmetry. 2011 ; Vol. 22, No. 2. pp. 246-251.
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